PT846683E - Derivados de 4-hidroxi-piperidina - Google Patents
Derivados de 4-hidroxi-piperidina Download PDFInfo
- Publication number
- PT846683E PT846683E PT97121040T PT97121040T PT846683E PT 846683 E PT846683 E PT 846683E PT 97121040 T PT97121040 T PT 97121040T PT 97121040 T PT97121040 T PT 97121040T PT 846683 E PT846683 E PT 846683E
- Authority
- PT
- Portugal
- Prior art keywords
- ylmethyl
- benzyl
- hydroxy
- dihydro
- compound
- Prior art date
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- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical class OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 136
- -1 2-imidazolyl Chemical group 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 33
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- 230000004770 neurodegeneration Effects 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- HQOGNACJOYOFGE-FQEVSTJZSA-N 1-[[(2s)-5-hydroxy-2,3-dihydro-1-benzofuran-2-yl]methyl]-4-[(4-methylphenyl)methyl]piperidin-4-ol Chemical compound C1=CC(C)=CC=C1CC1(O)CCN(C[C@H]2OC3=CC=C(O)C=C3C2)CC1 HQOGNACJOYOFGE-FQEVSTJZSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- SSYOSKXMPLDPGE-UHFFFAOYSA-N 1-[(5-hydroxy-2,3-dihydro-1h-inden-2-yl)methyl]-4-[(4-methylphenyl)methyl]piperidin-4-ol Chemical compound C1=CC(C)=CC=C1CC1(O)CCN(CC2CC3=CC(O)=CC=C3C2)CC1 SSYOSKXMPLDPGE-UHFFFAOYSA-N 0.000 claims description 6
- YZBGEAMUICZYRG-UHFFFAOYSA-N 2-[[4-hydroxy-4-[(4-methylphenyl)methyl]piperidin-1-yl]methyl]-1,2,3,4-tetrahydronaphthalene-1,6-diol Chemical compound C1=CC(C)=CC=C1CC1(O)CCN(CC2C(C3=CC=C(O)C=C3CC2)O)CC1 YZBGEAMUICZYRG-UHFFFAOYSA-N 0.000 claims description 6
- CVVJTYADYZAUJH-UHFFFAOYSA-N 2-[[4-hydroxy-4-[(4-methylphenyl)methyl]piperidin-1-yl]methyl]-2,3-dihydro-1h-indol-5-ol Chemical compound C1=CC(C)=CC=C1CC1(O)CCN(CC2NC3=CC=C(O)C=C3C2)CC1 CVVJTYADYZAUJH-UHFFFAOYSA-N 0.000 claims description 6
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims description 6
- GCSHHLMOSIPLJN-UHFFFAOYSA-N 2-[[4-hydroxy-4-[(4-methylphenyl)methyl]piperidin-1-yl]methyl]-2,3-dihydro-1h-indene-1,5-diol Chemical compound C1=CC(C)=CC=C1CC1(O)CCN(CC2C(C3=CC=C(O)C=C3C2)O)CC1 GCSHHLMOSIPLJN-UHFFFAOYSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 208000034189 Sclerosis Diseases 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000001580 bacterial effect Effects 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 238000006264 debenzylation reaction Methods 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- HPWCBURTSCWGFC-UHFFFAOYSA-N 1-[(6-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl]-4-[(4-methylphenyl)methyl]piperidin-4-ol Chemical compound C1=CC(C)=CC=C1CC1(O)CCN(CC2CC3=CC=C(O)C=C3CC2)CC1 HPWCBURTSCWGFC-UHFFFAOYSA-N 0.000 claims description 3
- BNSDZJZLEGLVBH-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-1-[(5-hydroxy-2,3-dihydro-1-benzofuran-2-yl)methyl]piperidin-4-ol Chemical compound C1C2=CC(O)=CC=C2OC1CN(CC1)CCC1(O)CC1=CC=C(F)C=C1 BNSDZJZLEGLVBH-UHFFFAOYSA-N 0.000 claims description 3
- VURSRIGJFVXQCE-UHFFFAOYSA-N 4-benzyl-1-[(5-hydroxy-2,3-dihydro-1-benzofuran-2-yl)methyl]piperidin-4-ol Chemical compound C1C2=CC(O)=CC=C2OC1CN(CC1)CCC1(O)CC1=CC=CC=C1 VURSRIGJFVXQCE-UHFFFAOYSA-N 0.000 claims description 3
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- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 2
- HQOGNACJOYOFGE-UHFFFAOYSA-N 1-[(5-hydroxy-2,3-dihydro-1-benzofuran-2-yl)methyl]-4-[(4-methylphenyl)methyl]piperidin-4-ol Chemical compound C1=CC(C)=CC=C1CC1(O)CCN(CC2OC3=CC=C(O)C=C3C2)CC1 HQOGNACJOYOFGE-UHFFFAOYSA-N 0.000 claims description 2
- PIBYADODKADFOZ-IBGZPJMESA-N 4-[(4-chlorophenyl)methyl]-1-[[(2s)-5-hydroxy-2,3-dihydro-1-benzofuran-2-yl]methyl]piperidin-4-ol Chemical compound C([C@H]1OC2=CC=C(C=C2C1)O)N(CC1)CCC1(O)CC1=CC=C(Cl)C=C1 PIBYADODKADFOZ-IBGZPJMESA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- SRMGHCDNIDDQJY-UHFFFAOYSA-N 2-[(4-benzyl-4-hydroxypiperidin-1-yl)methyl]-1,2,3,4-tetrahydronaphthalene-1,6-diol Chemical compound C1CC2=CC(O)=CC=C2C(O)C1CN(CC1)CCC1(O)CC1=CC=CC=C1 SRMGHCDNIDDQJY-UHFFFAOYSA-N 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
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- 230000018044 dehydration Effects 0.000 claims 1
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- 230000009385 viral infection Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 86
- 239000000203 mixture Substances 0.000 description 56
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 239000011734 sodium Substances 0.000 description 26
- 239000000284 extract Substances 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
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- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 12
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- VJDOQBNSKZDORJ-UHFFFAOYSA-N 2-(bromomethyl)-5-phenylmethoxy-2,3-dihydro-1-benzofuran Chemical compound C=1C=C2OC(CBr)CC2=CC=1OCC1=CC=CC=C1 VJDOQBNSKZDORJ-UHFFFAOYSA-N 0.000 description 10
- 102000014649 NMDA glutamate receptor activity proteins Human genes 0.000 description 10
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 10
- 210000000287 oocyte Anatomy 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
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- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 210000004556 brain Anatomy 0.000 description 5
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- ASFOGSWNTNOTCS-UHFFFAOYSA-N 2-[[4-[(4-methylphenyl)methyl]-4-phenylmethoxypiperidin-1-yl]methyl]-2,3-dihydro-1h-indene-1,5-diol Chemical compound C1=CC(C)=CC=C1CC1(OCC=2C=CC=CC=2)CCN(CC2C(C3=CC=C(O)C=C3C2)O)CC1 ASFOGSWNTNOTCS-UHFFFAOYSA-N 0.000 description 4
- DGNFSJPAWJLVOH-UHFFFAOYSA-N 4-[(4-methylphenyl)methyl]piperidin-4-ol Chemical compound C1=CC(C)=CC=C1CC1(O)CCNCC1 DGNFSJPAWJLVOH-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
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- Health & Medical Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96119345 | 1996-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT846683E true PT846683E (pt) | 2002-02-28 |
Family
ID=8223458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT97121040T PT846683E (pt) | 1996-12-03 | 1997-12-01 | Derivados de 4-hidroxi-piperidina |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6359138B1 (fr) |
| JP (1) | JP3045988B2 (fr) |
| KR (1) | KR100257947B1 (fr) |
| CN (2) | CN1086702C (fr) |
| AR (1) | AR009641A1 (fr) |
| AT (1) | ATE205830T1 (fr) |
| AU (1) | AU736597B2 (fr) |
| BR (1) | BR9705509B1 (fr) |
| CA (1) | CA2220649C (fr) |
| CO (1) | CO4910155A1 (fr) |
| CZ (1) | CZ376997A3 (fr) |
| DE (1) | DE69706813T2 (fr) |
| DK (1) | DK0846683T3 (fr) |
| ES (1) | ES2163086T3 (fr) |
| HR (1) | HRP970653B1 (fr) |
| ID (1) | ID17678A (fr) |
| IL (1) | IL122352A0 (fr) |
| MA (1) | MA24410A1 (fr) |
| NO (1) | NO975541L (fr) |
| NZ (1) | NZ329271A (fr) |
| PE (1) | PE20499A1 (fr) |
| PL (1) | PL323447A1 (fr) |
| PT (1) | PT846683E (fr) |
| RU (1) | RU2184112C2 (fr) |
| SG (1) | SG71062A1 (fr) |
| TR (1) | TR199701488A2 (fr) |
| UY (1) | UY24797A1 (fr) |
| YU (1) | YU46997A (fr) |
| ZA (1) | ZA9710653B (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU227197B1 (en) * | 2000-10-24 | 2010-10-28 | Richter Gedeon Nyrt | Nmda receptor antagonist carboxylic acid amide derivatives and pharmaceutical compositions containing them |
| ITMI20012060A1 (it) * | 2001-10-05 | 2003-04-05 | Recordati Chem Pharm | Nuovi eterocilcli n-acilati |
| US7005432B2 (en) * | 2002-05-16 | 2006-02-28 | Hoffman-La Roche Inc. | Substituted imidazol-pyridazine derivatives |
| EP1600447A1 (fr) * | 2004-05-28 | 2005-11-30 | Neuropharma S.A.U. | Inhibiteurs de butyrylcholinestérase selective |
| HUP0401522A2 (en) * | 2004-07-29 | 2006-04-28 | Richter Gedeon Vegyeszet | New 4-benzylidene-piperidine derivatives, pharmaceutical compositions containing the same and process for their preparation |
| TW200621677A (en) * | 2004-09-21 | 2006-07-01 | Astellas Pharma Inc | Cyclic amine derivative or salt thereof |
| KR101233223B1 (ko) * | 2004-12-21 | 2013-02-14 | 제이엔씨 석유 화학 주식회사 | 크로만환을 가지는 액정 화합물, 액정 조성물 및 이 액정조성물을 함유하는 액정 표시소자 |
| RU2538982C1 (ru) * | 2013-11-19 | 2015-01-10 | Федеральное Государственное Бюджетное Образовательное Учреждение Высшего Профессионального Образования "Нижегородский Государственный Университет Им. Н.И. Лобачевского" | Производное n-(1s)-1',2',3'-триметокси-6,7-дигидро-1н-бензо[5',6':5,4]циклогепта-[3,2-f]бензофуран-1-ил)ацетамида и его применение |
| EP3233077B1 (fr) * | 2014-12-19 | 2026-05-06 | The Broad Institute, Inc. | Ligands des récepteurs dopaminergiques d2 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE546389C (de) | 1927-12-30 | 1932-03-14 | Ralph Mayhew | Vorrichtung zur Bedienung von Tasteninstrumenten |
| US3476760A (en) | 1967-03-06 | 1969-11-04 | Smithkline Corp | Substituted piperidinoalkylthianaphthenes and benzofurans |
| US3506671A (en) * | 1967-11-01 | 1970-04-14 | Smithkline Corp | 1-naphthylalkyl-4-phenylpiperidine derivatives |
| US3557123A (en) * | 1967-11-01 | 1971-01-19 | Smith Kline French Lab | 1-naphthylalkyl-4-phenylpiperidine derivatives |
| US4016281A (en) | 1975-02-22 | 1977-04-05 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Tetralone and indanone compounds |
| DE2507782A1 (de) | 1975-02-22 | 1976-09-02 | Merck Patent Gmbh | Tetralon- und indanon-derivate sowie verfahren zu ihrer herstellung |
| US4039676A (en) | 1975-06-23 | 1977-08-02 | Ciba-Geigy Corporation | 2-piperidinoalkyl-1,4-benzodioxans |
| DE3660628D1 (en) * | 1985-02-01 | 1988-10-06 | Lafon Labor | 1-ethyl- 3-hydroxy-3-phenylpiperidine, process for its preparation and its therapeutical use |
| GB8515389D0 (en) | 1985-06-18 | 1985-07-17 | Ici Plc | Heterocyclic compounds |
| GB8515388D0 (en) | 1985-06-18 | 1985-07-17 | Ici Plc | Heterocyclic compounds |
| EP0554247B1 (fr) | 1990-05-10 | 2000-04-26 | Pfizer Inc. | Indolone neuroprotecteur et derives apparentes |
| AU655840B2 (en) * | 1991-07-17 | 1995-01-12 | Pfizer Inc. | 2-(4-hydroxypiperidino)-1-alkanol derivatives as antiischemic agents |
| DE4140542A1 (de) | 1991-12-09 | 1993-06-17 | Bayer Ag | Piperdylmethyl substituierte chormanderivate |
| US5436255A (en) | 1992-07-23 | 1995-07-25 | Pfizer Inc. | Method of treating diseases susceptable to treatment by blocking NMDA-receptors |
-
1997
- 1997-11-10 CA CA002220649A patent/CA2220649C/fr not_active Expired - Fee Related
- 1997-11-14 SG SG1997004062A patent/SG71062A1/en unknown
- 1997-11-24 US US08/976,540 patent/US6359138B1/en not_active Expired - Fee Related
- 1997-11-26 PE PE1997001073A patent/PE20499A1/es not_active Application Discontinuation
- 1997-11-26 ZA ZA9710653A patent/ZA9710653B/xx unknown
- 1997-11-27 IL IL12235297A patent/IL122352A0/xx unknown
- 1997-11-27 CZ CZ973769A patent/CZ376997A3/cs unknown
- 1997-11-27 NZ NZ329271A patent/NZ329271A/xx unknown
- 1997-11-27 YU YU46997A patent/YU46997A/sh unknown
- 1997-11-28 AR ARP970105596A patent/AR009641A1/es active IP Right Grant
- 1997-12-01 CO CO97070180A patent/CO4910155A1/es unknown
- 1997-12-01 MA MA24880A patent/MA24410A1/fr unknown
- 1997-12-01 JP JP9329891A patent/JP3045988B2/ja not_active Expired - Fee Related
- 1997-12-01 PT PT97121040T patent/PT846683E/pt unknown
- 1997-12-01 AT AT97121040T patent/ATE205830T1/de not_active IP Right Cessation
- 1997-12-01 UY UY24797A patent/UY24797A1/es unknown
- 1997-12-01 ES ES97121040T patent/ES2163086T3/es not_active Expired - Lifetime
- 1997-12-01 DK DK97121040T patent/DK0846683T3/da active
- 1997-12-01 DE DE69706813T patent/DE69706813T2/de not_active Expired - Lifetime
- 1997-12-02 NO NO975541A patent/NO975541L/no not_active Application Discontinuation
- 1997-12-02 PL PL97323447A patent/PL323447A1/xx unknown
- 1997-12-02 TR TR97/01488A patent/TR199701488A2/xx unknown
- 1997-12-02 AU AU46841/97A patent/AU736597B2/en not_active Ceased
- 1997-12-02 CN CN97123066A patent/CN1086702C/zh not_active Expired - Fee Related
- 1997-12-02 CN CNB011370645A patent/CN1162425C/zh not_active Expired - Fee Related
- 1997-12-02 BR BRPI9705509-3A patent/BR9705509B1/pt not_active IP Right Cessation
- 1997-12-02 ID IDP973819A patent/ID17678A/id unknown
- 1997-12-03 HR HR970653A patent/HRP970653B1/xx not_active IP Right Cessation
- 1997-12-03 KR KR1019970065495A patent/KR100257947B1/ko not_active Expired - Fee Related
- 1997-12-03 RU RU97120624/04A patent/RU2184112C2/ru not_active IP Right Cessation
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